Personally... I think all tatt's should have a strong meaning behind them. I've been toying with the idea of getting the name of a song on my arm or chest. My connection to the song is somewhat personal and it's relevant to who I am, therefore I can see myself never regretting it.
I could've gotten "Juggalo" or a hatchet man tatt for free on a few different occasions when I was 13-15/16. I always decided against it though. In the eyes of history, ICP and Psychopathic records aren't the best musicians to try and glorify through something so permanent.
Though, If I ever ran into Kat Von D or had the money to visit her, I'd probably get a Tupac portrait capped on my shoulder... and something from one of his songs.